This chapter examines a novel (NL. 26) of Leo VI (886–912) which permitted eunuchs to adopt children—thereby repealing Justinian I’s legal prohibition. Adoption, traditionally understood as a legally recognised form of kinship ‘by arrangement’, provided not only solace to the childless but also conferred tangible legal benefits to adopted children, such as rights of succession and dowry. For eunuchs, physically barred from biological reproduction, adoption thus represented the only possible avenue for having legitimate offspring. This chapter compares NL. 26 and its counterpart, NL. 27 (concerning women’s adoption), with earlier provisions to trace the transformation of adoption law within broader Byzantine legal and social developments. Particular attention is given to the Christianisation of adoption in other novels of Leo VI as a significant factor that explains why eunuchs’ adoption was permitted in NL. 26. The chapter further explores the concept used in the novel, namely that castrated individuals were considered deserving of compensation for the loss of their genitals and the childlessness through the process of adoption. This chapter presents the possibility that such a sympathetic notion also emerged primarily as a result of the changes in the character of adoption. Ultimately, it reveals a novel imperial attitude: eunuchs regarded as a kind of disabled individuals deserving sympathy.